Herbicidal compositions

ABSTRACT

Herbicides containing compositions of glycolic acid amides and other active ingredients.

This application is a division of application Ser. No. 627,965, filed Nov. 3, 1975, now U.S. Pat. No. 4,057,414, issued Nov. 8, 1977.

The present invention application relates to herbicides containing compositions of sulfonylglycolic acid amides or sulfonylglycolic acid imides.

It is known that pyridazones (German Pat. No. 1,105,232), benzofuranyl sulfonates (German Laid-Open Application DOS No. 1,926,139), benzofuranylalkylamino sulfonates (German Laid-Open Application DOS No. 2,324,592), azetidine carbothiolates (German Laid-Open Application DOS No. 2,312,045), fatty acids (German Pat. No. 959,066), thiol carbamates (U.S. Pat. No. 3,185,720; U.S. Pat. No. 3,330,821), carbamates (German Laid-Open Application DOS No. 1,567,151; German Printed Application DAS No. 1,137,255), pyrazolium compounds (German Laid-Open Application DOS No. 2,260,485), α-cyanoacrylates (German Laid-Open Application DOS No. 1,642,231), anilides (British Pat. No. 903,766) and 1,2,4-triazinones (German Laid-Open Application DOS No. 2,138,031) have a herbicidal action. However, this action is not always satisfactory.

We have now found that compositions of one or more of these active ingredients and sulfonylglycolic acid amides (German Laid-Open Applications DOS Nos. 2,201,432 and 2,334,715) or sulfonylglycolic acid imides (German Laid-Open Application DOS No. 2,219,923), which are known as individual herbicidal active ingredients, have an unforeseeably superior herbicidal action over their individual components.

These compositions consist of

(A) A GLYCOLIC ACID AMIDE OF THE FORMULA ##STR1## where X denotes ##STR2## R¹ denoting alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl or haloalkynyl of a maximum of 6 carbon atoms, alkoxyalkyl, haloalkoxyalkyl, alkenoxyalkyl, alkynoxyalkyl or cycloalkyl, and R² denoting phenyl which may bear one or more identical or different substituents, the number of substituents, which may be halogen, lower alkyl of a maximum of 4 carbon atoms, haloalkyl, alkoxy, alkylsulfonyl, alkylaminosulfonyl, cyano, hydroxy, nitro or amino, being from 0 to 3, and the carbonamide nitrogen being a ring member of an optionally bicyclic cycloalkylimine which may be substituted by halogen or lower alkyl; which may contain further hetero atoms in the ring, and which has a maximum of 9 carbon atoms, and Y denotes ##STR3## R³, R⁴, R⁵ and R⁶ denoting alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl or haloalkynyl of a maximum of 8 carbon atoms, unsubstituted or substituted phenyl or cycloalkyl of a maximum of 8 carbon atoms, and R⁴ and R⁵ additionally denoting hydrogen, and

(b) a 1,2,4-triazinone of the formula ##STR4## where X denotes hydrogen, methyl or trifluoromethyl and R¹ denotes methyl.

Examples of suitable components for compositions according to the invention are the active ingredients listed below:

    __________________________________________________________________________      ##STR5##                                                                      R.sup.1     R.sup.2                                                            __________________________________________________________________________     CH.sub.3    H                                                                  CH.sub.3    CH.sub.3                                                           CH.sub.3    C.sub.2 H.sub.5                                                    CH.sub.3    CH.sub.2 CH.sub.2 Cl                                               CH.sub.3    n-C.sub.3 H.sub.7                                                  CH.sub.3    i-C.sub.3 H.sub.7                                                  CH.sub.3    n-C.sub.4 H.sub.9                                                  CH.sub.3    sec-C.sub.4 H.sub.9                                                CH.sub.3    i-C.sub.4 H.sub.9                                                  CH.sub.3                                                                                    ##STR6##                                                          CH.sub.3                                                                                    ##STR7##                                                          CH.sub.3                                                                                    ##STR8##                                                          C.sub.2 H.sub.5                                                                            CH.sub.3                                                           C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                    C.sub.2 H.sub.5                                                                            CH.sub.2 CH.sub.2 Cl                                               C.sub.2 H.sub.5                                                                            n-C.sub.3 H.sub.7                                                  C.sub.2 H.sub.5                                                                            i-C.sub.3 H.sub.7                                                  n-C.sub.3 H.sub.7                                                                          CH.sub.3                                                           n-C.sub.3 H.sub.7                                                                          i-C.sub.3 H.sub.7                                                  C.sub.2 H.sub.5                                                                            H                                                                  i-C.sub.3 H.sub.7                                                                          H                                                                  i-C.sub.3 H.sub.7                                                                          CH.sub.3                                                           i-C.sub.3 H.sub.7                                                                          C.sub.2 H.sub.5                                                    i-C.sub.3 H.sub.7                                                                          CH.sub.2 CH.sub.2 Cl                                               i-C.sub.3 H.sub.7                                                                          n-C.sub.3 H.sub.7                                                  i-C.sub.3 H.sub.7                                                                          i-C.sub.3 H.sub.7                                                  i-C.sub.3 H.sub.7                                                                          n-C.sub.4 H.sub.9                                                  i-C.sub.3 H.sub.7                                                                          sec.-C.sub.4 H.sub.9                                               i-C.sub.3 H.sub.7                                                                           ##STR9##                                                          CH.sub.2CHCH.sub.2                                                                         CH.sub.3                                                           CH.sub.2CCH CH.sub.3                                                           CH.sub.2CCH i-C.sub.3 H.sub.7                                                  n-C.sub.4 H.sub.9                                                                          CH.sub.3                                                           n-C.sub.4 H.sub.9                                                                          C.sub.2 H.sub.5                                                    n-C.sub.4 H.sub.9                                                                          n-C.sub.3 H.sub.7                                                  n-C.sub.4 H.sub.9                                                                          i-C.sub.3 H.sub.7                                                  sec.-C.sub.4 H.sub.9                                                                       H                                                                  sec.-C.sub.4 H.sub.9                                                                       CH.sub.3                                                           sec.-C.sub.4 H.sub.9                                                                       C.sub.2 H.sub.5                                                    sec.-C.sub.4 H.sub.9                                                                       CH.sub.2 CH.sub.2 Cl                                               sec.-C.sub.4 H.sub.9                                                                       n-C.sub.3 H.sub.7                                                  sec.-C.sub.4 H.sub.9                                                                       i-C.sub.3 H.sub.7                                                  i-C.sub.4 H.sub.9                                                                          i-C.sub.3 H.sub.7                                                  tert.-C.sub.4 H.sub.9                                                                      CH.sub.3                                                           tert.-C.sub.4 H.sub.9                                                                      C.sub.2 H.sub.5                                                    tert- C.sub.4 H.sub.9                                                                      CH.sub.2 CH.sub.2 Cl                                               tert.-C.sub.4 H.sub.9                                                                      i-C.sub.3 H.sub.7                                                   ##STR10##  H                                                                   ##STR11##  CH.sub.3                                                            ##STR12##  C.sub.2 H.sub.5                                                     ##STR13##  CH.sub.2 CH.sub.2 Cl                                                ##STR14##  n-C.sub.3 H.sub.7                                                   ##STR15##  i-C.sub.3 H.sub.7                                                   ##STR16##  n-C.sub.4 H.sub.9                                                   ##STR17##  i-C.sub.3 H.sub.7                                                   ##STR18##                                                                     R.sup.1     R.sup.2        R.sup.3                                             __________________________________________________________________________      ##STR19##  CH.sub.3       CH.sub.3                                             ##STR20##  CH.sub.3       CH.sub.3                                             ##STR21##  CH.sub.3       CH.sub.3                                             ##STR22##  CH.sub.3       CH.sub.3                                             ##STR23##  CH.sub.3       C.sub.2 H.sub.5                                      ##STR24##  CH.sub.3       C.sub.2 H.sub.5                                      ##STR25##  CH.sub.3       C.sub.2 H.sub.5                                      ##STR26##  CH.sub.3       C.sub.2 H.sub.5                                      ##STR27##  CH.sub.3       i-C.sub.3 H.sub.7                                    ##STR28##  CH.sub.3       i-C.sub.3 H.sub.7                                    ##STR29##  CH.sub.3       i-C.sub.3 H.sub.7                                    ##STR30##  CH.sub.3       i-C.sub.3 H.sub.7                                    ##STR31##  CH.sub.3       i-C.sub.3 H.sub.7                                    ##STR32##  C.sub.2 H.sub.5                                                                               CH.sub.3                                             ##STR33##  C.sub.2 H.sub.5                                                                               C.sub.2 H.sub.5                                      ##STR34##  C.sub.2 H.sub.5                                                                               n-C.sub.3 H.sub.7                                    ##STR35##  C.sub.2 H.sub.5                                                                               i-C.sub.3 H.sub.7                                    ##STR36##  C.sub.2 H.sub.5                                                                               i-C.sub.3 H.sub.7                                    ##STR37##  i-C.sub.3 H.sub.7                                                                             CH.sub.3                                             ##STR38##  i-C.sub.3 H.sub.7                                                                             CH.sub.3                                             ##STR39##  i-C.sub.3 H.sub.7                                                                             C.sub.2 H.sub.5                                      ##STR40##  i-C.sub.3 H.sub.7                                                                             n-C.sub.3 H.sub.7                                    ##STR41##  i-C.sub.3 H.sub.7                                                                             i-C.sub.3 H.sub.7                                    ##STR42##  i-C.sub.3 H.sub.7                                                                             i-C.sub.3 H.sub.7                                    ##STR43##                                                                                  ##STR44##     i-C.sub.3 H.sub.7                                    ##STR45##                                                                     R.sup.3     R.sup.1        R.sup.2                                             __________________________________________________________________________     CH.sub.3    CH.sub.3       CH.sub.3                                            CH.sub.3    CH.sub.3       C.sub.2 H.sub.5                                     C.sub.2 H.sub.5                                                                            CH.sub.3       CH.sub.3                                            C.sub.2 H.sub.5                                                                            CH.sub.3       C.sub.2 H.sub.5                                     i-C.sub.3 H.sub.7                                                                          CH.sub.3       CH.sub.3                                            i-C.sub.3 H.sub.7                                                                          CH.sub.3       C.sub.2 H.sub.5                                     i-C.sub.3 H.sub.7                                                                          C.sub.2 H.sub.5                                                                               C.sub.2 H.sub.5                                     i-C.sub.3 H.sub.7                                                                          CH.sub.3       CH.sub.2 CH.sub.2 Cl                                sec.-C.sub.4 H.sub.9                                                                       CH.sub.3       CH.sub.3                                             ##STR46##                                                                     R.sup.1     R.sup.2                                                            __________________________________________________________________________     CH.sub.2C  CH                                                                              CH.sub.3                                                           i-C.sub.3 H.sub.7                                                                          C.sub.2 H.sub.5                                                    i-C.sub.3 H.sub.7                                                                          n-C.sub.3 H.sub.7                                                  i-C.sub.3 H.sub.7                                                                          i-C.sub.3 H.sub.7                                                  i-C.sub.3 H.sub.7                                                                          n-C.sub.4 H.sub.9                                                  tert.-C.sub.4 H.sub.9                                                                      CH.sub.3                                                           sec. -C.sub.4 H.sub.9                                                                      CH.sub.3                                                           i-C.sub.4 H.sub.9                                                                          CH.sub.3                                                            ##STR47##  CH.sub.3                                                            ##STR48##  CH.sub.3                                                            ##STR49##  C.sub.2 H.sub.5                                                     ##STR50##  n-C.sub.3 H.sub.7                                                   ##STR51##  i-C.sub.3 H.sub.7                                                   ##STR52##  n-C.sub.4 H.sub.9                                                   ##STR53##                                                                                  ##STR54##                                                          ##STR55##                                                                                  ##STR56##                                                         i-C.sub.3 H.sub.7                                                                          CH.sub.3                                                            ##STR57##  CH.sub.3                                                            ##STR58##                                                                     R.sup.1     R.sup.2        R.sup.3                                             __________________________________________________________________________      ##STR59##  CH.sub.2OCH.sub.3                                                                             CH.sub.3                                             ##STR60##  CH.sub.2OCH.sub.3                                                                             CH.sub.3                                             ##STR61##  CH.sub.2OCH.sub.3                                                                             CH.sub.3                                             ##STR62##  CH.sub.2OCH.sub.3                                                                             CH.sub.2 Cl                                          ##STR63##  CH.sub.2OCH.sub.3                                                                             C.sub.2 H.sub.5                                      ##STR64##  CH.sub.2OCH.sub.3                                                                             i-C.sub.3 H.sub.7                                    ##STR65##  CH.sub.2OCH.sub.3                                                                             CH.sub.3                                             ##STR66##  CH.sub.2OCH.sub.3                                                                             C.sub.2 H.sub.5                                      ##STR67##  CH.sub.2OC.sub.2 H.sub.5                                                                      CH.sub.3                                             ##STR68##  CH.sub.2OC.sub.2 H.sub.5                                                                      CH.sub.3                                             ##STR69##  CH.sub.2OC.sub.2 H.sub.5                                                                      C.sub.2 H.sub.5                                      ##STR70##  CH.sub.2OC.sub.2 H.sub.5                                                                      i-C.sub.3 H.sub.7                                    ##STR71##  CH.sub.2OC.sub.2 H.sub.5                                                                      CH.sub.3                                             ##STR72##  CH.sub.2 OC.sub.2 H.sub.5                                                                     CH.sub.2CH(CH.sub.3).sub.2                           ##STR73##  CH.sub.2OC.sub.3 H.sub.7 n                                                                    CH.sub.3                                             ##STR74##  CH.sub.2OC.sub.3 H.sub.7 n                                                                    C.sub.2 H.sub.5                                      ##STR75##  CH.sub.2OCH(CH.sub.3).sub.2                                                                   C.sub.2 H.sub.5                                      ##STR76##                                                                                  ##STR77##     C.sub.2 H.sub.5                                      ##STR78##  CH.sub.2OCH(CH.sub.3).sub.2                                                                   CH.sub.3                                             ##STR79##                                                                                  ##STR80##     CH.sub.3                                             ##STR81##  CH.sub.2OC.sub.3 H.sub.7 n                                                                    CH.sub.3                                             ##STR82##  CH.sub.2OCH(CH.sub.3).sub.2                                                                   CH.sub.3                                             ##STR83##  CH.sub.2OC.sub.3 H.sub.7 n                                                                    CH.sub.3                                             ##STR84##  CH.sub.2OCH.sub.2CHCH.sub.2                                                                   CH.sub.3                                             ##STR85##  CH.sub.2OCH.sub.2C CH                                                                         CH.sub.3                                             ##STR86##  CH.sub.2OCH(CH.sub.3).sub.2                                                                   CH.sub.3                                             ##STR87##  CH.sub.2OCH(CH.sub.3)C.sub.2 H.sub.5                                                          CH.sub.3                                             ##STR88##  CH.sub.2OC(CH.sub.3).sub.3                                                                    CH.sub.3                                             ##STR89##  CH.sub.2OCH(CH.sub.3)C.sub.2 H.sub.5                                                          C.sub.2 H.sub.5                                      ##STR90##  CH.sub.2OCH.sub.2CHCH.sub.2                                                                   CH.sub.3                                             ##STR91##  CH.sub.2OCH.sub.2CH(CH.sub. 3).sub.2                                                          CH.sub.3                                             ##STR92##                                                                     R           n                                                                  __________________________________________________________________________     CH.sub.3    4                                                                  C.sub.2 H.sub.5                                                                            4                                                                  CH.sub.2 CH.sub.2 Cl                                                                       4                                                                  i-C.sub.3 H.sub.7                                                                          4                                                                  n-C.sub.3 H.sub.7                                                                          4                                                                  n-C.sub.4 H.sub.9                                                                          4                                                                  sec.-C.sub.4 H.sub.9                                                                       4                                                                  i-C.sub.4 H.sub.9                                                                          4                                                                  CH.sub.3    5                                                                  C.sub.2 H.sub.5                                                                            5                                                                  n-C.sub.3 H.sub.7                                                                          5                                                                  i-C.sub.3 H.sub.7                                                                          5                                                                  n-C.sub.4 H.sub.9                                                                          5                                                                  CH.sub.3    6                                                                  C.sub.2 H.sub.5                                                                            6                                                                  CH.sub.2 CH.sub.2 Cl                                                                       6                                                                  n-C.sub.3 H.sub.7                                                                          6                                                                  i-C.sub.3 H.sub.7                                                                          6                                                                  n-C.sub.4 H.sub.9                                                                          6                                                                  sec.-C.sub.4 H.sub.9                                                                       6                                                                  CH(C.sub.2 H.sub.5).sub.2                                                                  6                                                                  CH.sub.2CH(CH.sub.3)C.sub.2 H.sub.5                                                        6                                                                  CH.sub.3    7                                                                  C.sub.2 H.sub.5                                                                            7                                                                  i-C.sub.3 H.sub.7                                                                          7                                                                  n-C.sub.3 H.sub.7                                                                          7                                                                  CH.sub.2CH.sub.2Cl                                                                         7                                                                  H           8 (bicyclo)                                                        CH.sub.3    8 (bicyclo)                                                        C.sub.2 H.sub.5                                                                            8 (bicyclo)                                                        i-C.sub.3 H.sub.7                                                                          8 (bicyclo)                                                        n-C.sub.3 H.sub.7                                                                          8 (bicyclo)                                                        n-C.sub.4 H.sub.9                                                                          8 (bicyclo)                                                        sec.-C.sub.4 H.sub.9                                                                       8 (bicyclo)                                                        i-C.sub.4 H.sub.9                                                                          8 (bicyclo)                                                         ##STR93##                                                                     R.sup.1     R.sup.2                                                            __________________________________________________________________________      ##STR94##  CH.sub.3                                                            ##STR95##  C.sub.2 H.sub.5                                                     ##STR96##  n-C.sub.3 H.sub.7                                                   ##STR97##  i-C.sub.3 H.sub.7                                                   ##STR98##  n-C.sub.4 H.sub.9                                                   ##STR99##  CH.sub.2CHCH.sub.2                                                  ##STR100## i-C.sub.3 H.sub.5                                                   ##STR101## C.sub.2 H.sub.5                                                     ##STR102## CH.sub.3                                                            ##STR103## C.sub.2 H.sub.5                                                     ##STR104## i-C.sub.3 H.sub.7                                                   ##STR105## C.sub.2 H.sub.5                                                     ##STR106## i-C.sub.3 H.sub.7                                                   ##STR107## CH.sub.3                                                            ##STR108## C.sub.2 H.sub.5                                                     ##STR109## n-C.sub.3 H.sub.7                                                   ##STR110## i-C.sub.3 H.sub.7                                                   ##STR111##                                                                    X           R.sup.1                                                            __________________________________________________________________________     H           CH.sub.3                                                           CH.sub.3    CH.sub.3                                                           CH.sub.3    CH.sub.3                                                           __________________________________________________________________________

sulfurous acid esters of glycolic acid amides, azetidine carbothioates and butynyl carbamates may also be used as components in addition to the active ingredients listed above.

The sulfurous acid esters of glycolic acid amides (a) may be obtained by reacting a glycolic acid amide with an alkyl chlorosulfinate at 10° to 15° C. in an inert solvent and in the presence of an agent capable of binding hydrogen chloride.

For instance, O-ethyl-O-(1-carbonylmethylazacycloheptane)-sulfite may be prepared by dripping a solution of 12.9 parts by weight of ethyl chlorosulfinate in 50 parts by weight of benzene at 10° to 15° C. into 15.7 parts by weight of glycolic acid hexamethylene amide dissolved together with 8 parts by weight of pyridine in 50 parts by weight of dry benzene. After 30 minutes the precipitated pyridinium hydrochloride is filtered off and the organic phase washed with water. After drying has been effected, the benzene is distilled off. There is obtained 20.4 parts by weight of the desired product. The compound has the following structure: ##STR112## n₂₅ = 1.4910.

The following active ingredients may for example be used:

N-methylacetanilido-(α-ethylsulfite)

N-methylacetanilido-(α-isopropylsulfite)

N-(butyn-1-yl-3)-acetanilido-(α-ethylsulfite)

N-(butyn-1-yl-3)-acetanilido-(α-isopropylsulfite)

N-(butyn-1-yl-3)-acetanilido-(α-methylsulfite) m.p.: 69° to 70° C.

N-isopropylacetanilido-(α-methylsulfite) m.p.: 60° to 61° C.

N-ethylacetanilido-(α-propylsulfite) n₂₅ ^(D) : 1.5295

N-ethylacetanilido-(α-isopropylsulfite) n₂₅ ^(D) : 1.5164

N-ethylacetanilido-(α-methylsulfite) n₂₅ ^(D) : 1.5118

N-ethylacetanilido-(α-ethylsulfite) n₂₅ ^(D) : 1.5010

N-methyl-(4-methoxyacetanilido)-(α-isopropylsulfite)

N-(butyn-1-yl-3)-methoxyacetanilido)-(α-isopropylsulfite)

N-methyl-(p-methylacetanilido)-(α-isopropylsulfite)

N-butyn-1-yl-3)-(p-methylacetanilido)-(α-isopropylsulfite)

N-(2-methylbenzyl)-acetanilido-(α-methylsulfite)

N-(2-methylbenzyl)-acetanilido-(α-ethylsulfite)

N-(2-methylbenzyl)-acetanilido-(α-propylsulfite)

N-(2-methylbenzyl)-acetanilido-(α-isopropylsulfite)

N-tert-butylacetanilido-(α-isopropylsulfite) m.p.: 78° C.

N-tert-butylacetanilido-(α-methylsulfite) m.p.: 57° C.

N-methylacetanilido-(α-sec-butylsulfite), n₂₅ = 1.5083

N-(butyn-1-yl-3)-acetanilido-(α-isobutylsulfite) n₂₅ : 1.5098

N-(butyn-1-yl-3)-acetanilido-(α-sec-butylsulfite) n₂₅ : 1.5132

N-(butyn-1-yl-3)-acetanilido-(α-n-butylsulfite) n₂₅ : 1.5172

N-isobutylacetanilido-(α-methylsulfite) n₂₅ : 1.5229

N-isobutylacetanilido-(α-ethylsulfite) n₂₅ : 1.5100

N-methylacetanilido-(α-n-butylsulfite) n₂₅ : 1.5144

N-isobutylacetanilido-(α-propylsulfite) n₂₅ : 1.5059

N-isobutylacetanilido-(α-isopropylsulfite) n₂₅ : 1.5028

N-methylacetanilido-(α-methylsulfite)

N-methylacetanilido-(α-isobutylsulfite)

N-(butyn-1-yl-3)-acetanilido-(α-methylsulfite)

N-methyl-(2-methylacetanilido)-(α-methylsulfite)

N-methyl-(4-methylacetanilido)-(α-methylsulfite)

N-methyl-(4-methoxyacetanilido)-(α-methylsulfite)

N-methyl-(3-chloroacetanilido)-(α-methylsulfite)

N-methyl-(2-methylacetanilido)-(α-ethylsulfite)

N-methylacetanilido-[α-(1-methyl-2-methoxy)-ethylsulfite]

N-methyl-(4-methylacetanilido)-(α-ethylsulfite)

N-methyl-(4-methoxyacetanilido)-(α-ethylsulfite)

N-methyl-(3- chloroacetanilido)-(α-ethylsulfite)

N-methyl-(2-methylacetanilido)-(α-isopropylsulfite)

N-methyl-(3-chloroacetanilido)-(α-isopropylsulfite)

N-methyl-(4-methylacetanilido)-(α-n-butylsulfite)

O-methyl-O-(1-carbonylmethylazacycloheptane)-sulfite; n₂₅ = 1.4955

O-isopropyl-O-(1-carbonylmethylazacycloheptane)-sulfite; n₂₅ = 1.4695

O-butyl-O-(1-carbonylmethylazacycloheptane)-sulfite; n₂₅ = 1.4875

O-propyl-O-(1-carbonylmethylazacycloheptane)-sulfite; n₂₅ = 1.4828

O-isopropyl-O-(1-carbonylmethylazacycloheptane)-sulfite; m.p. = 58° to 59° C.

O-ethyl-O-(1-carbonylmethyl-2-methylazacycloheptane)-sulfite; n₂₅ = 1.4882

O-isopropyl-O-(1-carbonylmethyl-2-methylazacycloheptane)-sulfite; n₂₅ = 1.4740

O-methyl-O-(1-carbonylmethyl-2,3-dimethylazacycloheptane)-sulfite; n₂₅ = 1.4952

O-ethyl-O-(1-carbonylmethyl-2,3-dimethylazacycloheptane)-sulfite; n₂₅ = 1.4860

O-propyl-O-(1-carbonylmethyl-2,3-dimethylazacycloheptane)-sulfite; n₂₅ = 1.4849

O-isopropyl-O-(1-carbonylmethyl-2,3-dimethylazacycloheptane)-sulfite; n₂₅ = 1.4749

O-ethyl-O-(1-carbonylmethyl-3,5,5-trimethyl-(3,3,5-trimethyl)-azacycloheptane)-sulfite; n₂₅ = 1.4850

(1:1 isomer mixture of the 3,3,5- and 3,5,5-trimethyl derivative)

O-isopropyl-O-(1-carbonylmethyl-3-methyl-(2-methyl)-azacycloheptane)-sulfite; n₂₅ = 1.4735

(isomer mixture, 55% of which being the 3-methyl and 45% of which the 2-methyl derivative)

O-ethyl-O-(1-carbonylmethylazacycloheptane)-sulfite

O-n-propyl-O-(1-carbonylmethylazacycloheptane)-sulfite

O-methyl-O-(1-carbonylmethyl-3-methylazacycloheptane)-sulfite

O-ethyl-O-(1-carbonylmethyl-3-methylazacycloheptane)-sulfite

O-isopropyl-O-(1-carbonylmethyl-3-methylazacycloheptane)-sulfite

O-ethyl-O-(1-carbonylmethyl-4-methylazacycloheptane)-sulfite

O-isopropyl-O-(1-carbonylmethyl-4-methylazacycloheptane)-sulfite

O-methyl-(1-carbonylmethyl-3-azabicyclo-[3,2,0]-heptane)-sulfite

O-ethyl-(1-carbonylmethyl-3-azabicyclo-[3,2,0]-heptane)-sulfite

O-n-propyl-(1-carbonylmethyl-3-azabicyclo-[3,2,0]-heptane)-sulfite

O-isopropyl-(1-carbonylmethyl-3-azabicyclo-[3,2,0]-heptane)-sulfite

O-isopropyl-O-(1-carbonylmethyl-2-methyl-(3-methyl)-azacycloheptane)-sulfite; n₂₅ = 1.4698

(isomer mixture, 75% of which is the 2-methyl and 25% of which the 3-methyl derivative)

O-allyl-O-(1-carbonylmethyl-2,3-dimethylazacycloheptane)-sulfite; n₂₅ = 1.4970

O-allyl-O-(1-carbonylmethylazacycloheptane)-sulfite; n₂₅ = 1.5026

O-(butyn-1-yl-3)-O-(1-carbonylmethyl-2,3-dimethylazacycloheptane)-sulfite; n₂₅ = 1.4929

O-(butyn-1-yl-3)-O-(1-carbonylmethyl-3-methylazacycloheptane)-sulfite; n₂₅ = 1.4965

O-ethyl-O-(1-carbonylmethylazacyclohexane)-sulfite

O-isopropyl-O-(1-carbonylmethylazacyclohexane)-sulfite

O-methyl-O-(1-carbonylmethyl-2-methylazacyclohexane)-sulfite

O-allyl-O-(1-carbonylmethyl-2-methylazacyclohexane)-sulfite

O-isopropyl-O-(1-carbonylmethyl-2-methylazacyclohexane)-sulfite

O-isopropyl-O-(1-carbonylmethyl-3-methylazacyclohexane)-sulfite

O-(β-chloroethyl)-O-(1-carbonylmethyl-3-methylazacyclohexane)-sulfite

O-ethyl-O-(1-carbonylmethyl-4-methylazacyclohexane)-sulfite

O-allyl-O-(1-carbonylmethyl-4-methylazacyclohexane)-sulfite

O-(β-chloroethyl)-O-(1-carbonylmethyl-4-methylazacyclohexane)-sulfite

O-methyl-O-(1-carbonylmethyl-3,3-dimethylazacyclohexane)-sulfite

O-isopropyl-O-(1-carbonylmethyl-3,3-dimethylazacyclohexane)-sulfite

O-(β-chloroethyl)-O-(1-carbonylmethyl-3,5,5-trimethyl)-(3,3,5-trimethylazacycloheptane)-sulfite

(1:1 isomer mixture of the 3,5,5- and the 3,3,5-trimethyl derivative).

A component may make up from 5 to 95 wt%, preferably 20 to 80 wt%, of an active ingredient composition according to the invention.

The amount used of the agents according to the invention may vary and depends in essence on the type of effect to be achieved; it is generally from 0.1 to 15 (and more), preferably from 0.2 to 6, kg per hectare of active ingredient. The agents according to the invention may be used once or several times before of after planting, before sowing, and before, during or after emergence of the crop plant and unwanted plants.

Application may be effected for instance in the form of directly sprayable solutions, powders, suspensions, (including high-percentage oily or aqueous suspensions) dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used; in any case they should ensure a fine distribution of the active ingredient.

For the preparation of solutions, emulsions, pastes and oil dispersions to be sprayed direct, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils, etc. and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons such as benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc. are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes, oil dispersions or wettable powders by adding water. To prepare emulsions, pastes and oil dispersions the ingredients as such or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.

Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ether, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonyphenol, alkylphenol polyglycol ethers, tributylphenol polyglycol ethers, alkylaryl polyester alcohols, isotridecyl alcohols, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulfite waste liquors and methyl cellulose.

Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silica gel, silicic acid, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.

The formulations contain from 0.1 to 95, and preferably 0.5 to 90%, by weight of active ingredient.

There may be added to the compositions or individual active ingredients (if desired, immediately before use (tankmix)) oils of various types, wetting agents or adherents, herbicides, fungicides, nematocides, insecticides, bactericides, trace elements, fertilizers, antifoams (e.g., silicones), growth regulators, antidotes and other herbicidally effective compounds such as

substituted anilines

substituted aryloxycarboxylic acids and salts, esters and amides thereof,

substituted ethers

substituted arsonic acids and their salts, esters and amides

substituted benzimidazoles

substituted benzisothiazoles

substituted benzothiadiazinone dioxides

substituted benzoxazines

substituted benzoxazinones

substituted benzothiadiazoles

substituted biurets

substituted quinolines

substituted carbamates

substituted aliphatic carboxylic acids and their salts, esters and amides

substituted aromatic carboxylic acids and their salts, esters and amides

substituted carbamoylalkylthiol- or -dithiophosphates

substituted quinazolines

substituted cycloalkylamidocarbothiolic acids and their salts, esters and amides

substituted cycloalkylcarbonamidothiazoles

substituted dicarboxylic acids and their salts, esters and amides

substituted dihydrobenzofuranyl sulfonates

substituted disulfides

substituted dipyridylium salts

substituted dithiocarbamates

substituted dithiophosphoric acids and their salts, esters and amides

substituted ureas

substituted hexahydro-1H-carbothioates

substituted hydantoins

substituted hydrazides

substituted hydrazonium salts

substituted isoxazole pyrimidones

substituted imidazoles

substituted isothiazole pyrimidones

substituted ketones

substituted naphthoquinones

substituted aliphatic nitriles

substituted aromatic nitriles

substituted oxadiazoles

substituted oxadiazinones

substituted oxadiazolidine diones

substituted oxadiazine diones

substituted phenols and their salts and esters

substituted phosphonic acids and their salts, esters and amides

substituted phosphonium chlorides

substituted phosphonalkyl glycines

substituted phosphites

substituted phosphoric acids and their salts, esters and amides

substsitutes piperidines

substituted pyrazoles

substituted pyrazole alkylcarboxylic acids and their salts, esters and amides

substituted pyrazolium salts

substituted pyrazolium alkyl sulfates

substituted pyridazines

substituted pyridazones

substituted pyridine carboxylic acids and their salts, esters and amides

substituted pyridines

substituted pyridine carboxylates

substituted pyridinones

substituted pyrimidines

substituted pyrimidones

substituted pyrrolidine carboxylic acid and its salts, esters and amides

substituted pyrrolidines

substituted pyrrolidones

substituted arylsulfonic acids and their salts, esters and amides

substituted styrenes

substituted tetrahydrooxadiazine diones

substituted tetrahydroxadiazole diones

substituted tetrahydromethanoindenes

substituted tetrahydroxadiazole thiones

substituted tetrahydrothiadiazine thiones

substituted tetrahydrothiadiazole diones

substituted aromatic thiocarbonylamides

substituted thiocarboxylic acids and their salts, esters and amides

substituted thiol carbamates

substituted thioureas

substituted thiophosphoric acids and their salts, esters and amides

substituted triazines

substituted triazoles

substituted uracils, and

substituted uretidine diones.

The last-mentioned herbicidal compounds may also be applied before or after the compositions according to the invention.

These agents may be added to the compositions according to the invention in a ratio by weight of from 1:10 to 10:1. The same applies to oils, fungicides, nematocides, insecticides, bactericides, antidotes and growth regulators.

The new compositions have a strong herbicidal action and may therefore be used as weedkillers or for controlling the growth of unwanted plants. Whether the new active ingredients are used as total or selective agents depends in essence on the amount of ingredient used per unit area.

By weeds and unwanted plant growth are meant all monocotyledonous and dicotyledonous plants which grow in loci where they are not desired.

The agents according to the invention may therefore be used for controlling for instance

    ______________________________________                                         Gramineae, such as                                                             Cynodon spp.        Dactylis spp.                                              Digitaria spp.      Avena spp.                                                 Echinochloa spp.    Bromus spp.                                                Setaria spp.        Uniola spp.                                                Panicum spp.        Poa spp.                                                   Alopecurus spp.     Leptochloa spp.                                            Lolium spp.         Brachiaria spp.                                            Sorghum spp.        Eleusine spp.                                              Agropyron spp.      Cenchrus spp.                                              Phalaris spp.       Eragrostis spp.                                            Apera spp.          Phragmites communis                                        etc.;                                                                          Cyperaceae, such as                                                            Carex spp.          Eleocharis spp.                                            Cyperus spp.        Scirpus spp.                                               etc.;                                                                          dicotyledonous weeds, such as                                                  Malvaceae, e.g.                                                                Abutilon theoprasti Hibiscus spp.                                              Sida spp.           Malva spp.                                                 etc.;                                                                          Compositae, such as                                                            Ambrosia spp.       Centaurea spp.                                             Lactuca spp.        Tussilago spp.                                             Senecio spp.        Lapsana communis                                           Sonchus spp.        Tagetes spp.                                               Xanthium spp.       Erigeron spp.                                              Iva spp.            Anthemis spp.                                              Galinsoga spp.      Matricaria spp.                                            Taraxacum spp.      Artemisia spp.                                             Chrysanthemum spp.  Bidens spp.                                                Cirsium spp.        etc.;                                                      Convolvulaceae, such as                                                        Convolvulus spp.    Cuscuta spp.                                               Ipomoea spp.        Jaquemontia tamnifolia                                     etc.;                                                                          Cruciferae, such as                                                            Barbarea vulgris    Arabidopsis thaliana                                       Brassica spp.       Descurainia spp.                                           Capsella spp.       Draba spp.                                                 Sisymbrium spp.     Coronopus didymus                                          Thlaspi spp.        Lepidium spp.                                              Sinapis arvensis    Raphanus spp.                                              etc.;                                                                          Geraniaeceae, such as                                                          Erodium spp.        Geranium spp.                                              etc.;                                                                          Portulacaceae, such as                                                         Portulaca spp.      etc.;                                                      Primalaceae, such as                                                           Anagallis arvensis  Lysimachia spp.                                            etc.;                                                                          Rubiaceae, such as                                                             Richardia spp.      Diodia spp.                                                Galium spp.         etc.;                                                      Scrophulariacea, such as                                                       Linaria spp.        Digitalis spp.                                             Veronica spp.       etc.;                                                      Solanaceae, such as                                                            Physalis spp.       Nicandra spp.                                              Solanum spp.        Datura spp.                                                etc.;                                                                          Urticaceae, such as                                                            Urtica spp.                                                                    Violaceae, such as                                                             Viola spp.          etc.;                                                      Zygophyllaceae, such as                                                        Tribulus terrestris etc.;                                                      Euphorbiaceae, such as                                                         Mercurialis annua   Euphorbia spp.                                             Umbelliferae, such as                                                          Daucus carota       Ammi majus                                                 Aethusa cynapium    etc.;                                                      Commelinaceae, such as                                                         Commelina spp.      etc.;                                                      Labiatae, such as                                                              Lamium spp.         Galeopsis spp.                                             etc.;                                                                          Leguminosae, such as                                                           Medicago spp.       Sesbania exaltata                                          Trifolium spp.      Cassia spp.                                                Vicia spp.          Lathyrus spp.                                              etc.;                                                                          Plantaginaceae, such as                                                        Plantago spp.       etc.;                                                      Polygonaceae, such as                                                          Polygonum spp.      Fagopyrum spp.                                             Rumex spp.          etc.;                                                      Aizoaceae, such as                                                             Mollugo verticillata                                                                               etc.;                                                      Amaranthaceae, such as                                                         Amaranthus spp.     etc.;                                                      Boraginaceae, such as                                                          Amsinckia spp.      Anchusa spp.                                               Myostis spp.        Lithospermum spp.                                          etc.;                                                                          Caryophyllaceae, such as                                                       Stellaria spp.      Silene spp.                                                Spergula spp.       Cerastium spp.                                             Saponaria spp.      Agrostemma githago                                         Scleranthus annuus  etc.;                                                      Chenopodiaceae, such as                                                        Chenopodium spp.    Atriplex spp.                                              Kochia spp.         Monolepsis nuttalliana                                     Salsola Kali        etc.;                                                      Lythraceae, such as                                                            Cuphea spp.         etc.;                                                      Oxalidaceae, such as                                                           Oxalis spp.                                                                    Ranunculaceae, such as                                                         Ranunculus spp.     Adonis spp.                                                Delphinium spp.     etc.;                                                      Papaveraceae, such as                                                          Papaver spp.        Fumaria offinicalis                                        etc.;                                                                          Onagraceae, such as                                                            Jussiaea spp.       etc.;                                                      Rosaceae, such as                                                              Alchemillia spp.    Potentilla spp.                                            etc.;                                                                          Potamogetonaceae, such as                                                      Potamogeton spp.    etc.;                                                      Najadaceae, such as                                                            Najas spp.          etc.;                                                      Equisetaceae                                                                   Equisetum spp.      etc.;                                                      Marsileaceae, such as                                                          Marsilea quadrifolia                                                                               etc.;                                                      Polypodiaceae,                                                                 Pteridium quilinum                                                             Alismataceae, such as                                                          Alisma spp.         Sagittaria sagittifolia                                    etc.                                                                            The herbicides according to the invention may be employed                     in cereal crops such as                                                        Avena spp.          Sorghum                                                    Triticum spp.       Zea mays                                                   Hordeum spp.        Panicum miliaceum                                          Secale spp.         Oryza spp.                                                 Saccharum offinicarum                                                          and in dicotyledon crops such as                                               Cruciferae, e.g.                                                               Brassica spp.       Raphanus spp.                                              Sinapis spp.        Lepidium spp.                                              Compositae, e.g.                                                               Lactuca spp.        Carthamus spp.                                             Helianthus spp.     Scorzonera spp.                                            Malvaceae, e.g.                                                                Gossypium hirsutum                                                             Leguminosae, e.g.                                                              Medicago spp.       Phaseolus spp.                                             Trifolium spp.      Arachis spp.                                               Pisum spp.          Glycine max.                                               Chenopodiaceae, e.g.                                                           Beta vulgaris                                                                  Spinacia spp.                                                                  Solanaceae, e.g.                                                               Solanum spp.        Capsicum annuum                                            Nicotiania spp.                                                                Linaceae, e.g.                                                                 Linum spp.                                                                     Umbelliferae, e.g.                                                             Petroselinum spp.   Apium graveolens                                           Daucus carota                                                                  Rosaceae, e.g.       Fragaria                                                  Cucurbitaceae, e.g.                                                            Cucumis spp.        Cucurbita spp.                                             Liliaceae, e.g.                                                                Allium spp.                                                                    Vitaceae, e.g.                                                                 Vitis vinifera                                                                 Bromeliaceae, e.g.                                                             Ananas sativus.                                                                ______________________________________                                    

The compositions may also be used as total agents on ditches, aquatic areas, railway track, waste and barren land, etc.

The compositions according to the invention were tested in the greenhouse and in the open. Their action corresponds to that of the compositions employed in the following examples.

EXAMPLE 1

In the greenhouse, loamy sandy soil was filled into pots and sown with various seeds. The soil prepared in this manner was then treated with the following amounts of the following individual ingredients and compositions thereof as dispersions or emulsions:

Iii -- o-(methylaminosulfonyl)-glycolic acid-N-isopropylanilide

Xxiv -- o-(methylaminosulfonyl)-glycolic acid hexamethylene amide

Lxi -- 3-(n-isopropylaminosulfonyloxyacetyl)-3-azabicyclo-(3,2,2)-nonane

Lxix -- 3-methyl-4-amino-5H-6-phenyl-1,2,4-triazin-5-one each at rates of 0.5, 1, 1.5, 2, 3 and 4 kg/ha,

Iii+lxix, xxiv+lxix and LXI+LXIX -- each at rates of 1+1, 1.5+0.5, 0.5+1.5, 1.5+1.5, 2+1 and 1+2 kg/ha.

After 4 to 5 weeks it was ascertained that, at the lower application rates, the compositions had a better herbicidal action than their components, combined with the same crop plant compatibility. At the higher rates, the compositions had a strong herbicidal action.

The results are given below:

    __________________________________________________________________________     Active ingredient                                                                          I              III                                                 kg/ha       0.5                                                                              1 1.5                                                                              2  3  4  0.5                                                                              0.5                                                                              1.5                                                                              2  3  4                                       Crop plants:                                                                   Beta vulgaris                                                                               0                                                                                0                                                                                0                                                                                0  0  10                                                                                0                                                                                0                                                                                0                                                                                0  0 10                                      Unwanted plants:                                                               Avena fatua  5                                                                               12                                                                               15                                                                               20 40  75                                                                               15                                                                               40                                                                               45                                                                               54 75 80                                      Echinochloa crus-galli                                                                      6                                                                               13                                                                               20                                                                               32 65  75                                                                               25                                                                               70                                                                               90                                                                               100                                                                               100                                                                               100                                     Stellaria media                                                                            20                                                                               45                                                                               60                                                                               80 95 100                                                                               10                                                                               25                                                                               45                                                                               55 65 70                                      Galium aparine                                                                             15                                                                               40                                                                               50                                                                               75 85  90                                                                               10                                                                               15                                                                               25                                                                               30 40 43                                      Chenopodium album                                                                          25                                                                               40                                                                               60                                                                               80 95 100                                                                               15                                                                               20                                                                               35                                                                               45 50 57                                      Alopecurus myosuroides                                                                      6                                                                               11                                                                               19                                                                               22 30  45                                                                               20                                                                               50                                                                               90                                                                               100                                                                               100                                                                               100                                     Lamium amplexicaule                                                                        10                                                                               20                                                                               25                                                                               40 70  90                                                                               10                                                                               20                                                                               35                                                                               55 60 70                                      Active ingredient                                                                          XXIV            LXI                                                Beta vulgaris                                                                               0                                                                                0                                                                                0                                                                                0  5  10                                                                                0                                                                                0                                                                                0                                                                                0  5 12                                      Avena fatua 25                                                                               60                                                                               75                                                                               80 90 100                                                                               25                                                                               40                                                                               60                                                                               65 80 90                                      Echinochloa crus-galli                                                                     35                                                                               60                                                                               90                                                                               100                                                                               100                                                                               100                                                                               50                                                                               70                                                                               90                                                                               95 100                                                                               100                                     Stellaria media                                                                            25                                                                               50                                                                               75                                                                               85 95 100                                                                               10                                                                               20                                                                               40                                                                               50 70 80                                      Galium aparine                                                                             25                                                                               40                                                                               50                                                                               65 75  85                                                                                5                                                                               10                                                                               15                                                                               30 50 65                                      Chenopodium album                                                                          30                                                                               40                                                                               45                                                                               60 70  90                                                                               10                                                                               20                                                                               25                                                                               35 50 70                                      Alopecurus myosuroides                                                                     40                                                                               75                                                                               90                                                                               95 100                                                                               100                                                                               40                                                                               60                                                                               85                                                                               95 100                                                                               100                                     Lamium amplexicaule                                                                        25                                                                               50                                                                               70                                                                               80 95 100                                                                               10                                                                               15                                                                               20                                                                               40 60 70                                      Active ingredient                                                                          LXIX                                                               kg/ha       0.5                                                                               1  1.5                                                                               2  3  4                                                   Beta vulgaris                                                                               0  0  0  0  0                                                     Avena fatua 10 15 25 40 50 65                                                  Echinochloa crus-galli                                                                     15 25 35 50 70 80                                                  Stellaria media                                                                            10 20 30 40 50 75                                                  Galium aparine                                                                             10 20 24 30 45 60                                                  Chenopodium album                                                                          15 30 40 55 70 85                                                  Alopecurus myosuroides                                                                     20 30 40 50 65 80                                                  Lamium amplexicaule                                                                        20 30 35 60 75 90                                                  Active ingredient                                                                          III + LXIX        XXIV + LXIX                                                     1.5+                                                                              0.5+                                                                              1.5+        1.5+                                                                              0.5+                                                                              1.5+                                    kg/ha       1+1                                                                               0.5                                                                               1.5                                                                               1.5                                                                               2+1                                                                               1+2                                                                               1+1                                                                               0.5                                                                               1.5                                                                               1.5                                                                               2+1                                                                               1+1                               Beta vulgaris                                                                              0  0  0  0  0  0  0  0  0  0  0  0                                 Avena fatua 95 95 80 100                                                                               100                                                                                92                                                                               100                                                                               100                                                                                90                                                                               100                                                                               100                                                                               100                               Echinochloa crus-galli                                                                     100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                               Stellaria media                                                                            85 95 80 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                                95                                                                               100                                                                               100                                                                               100                               Galium aparine                                                                             75 75 75  90                                                                                90                                                                               100                                                                               100                                                                               100                                                                                90                                                                               100                                                                               100                                                                               100                               Chenopodium album                                                                          90 90 95 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                               Alopecurus myosuroides                                                                     100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                               Lamium amplexicaule                                                                        90 95 85 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                               Active ingredient                                                                          LXI + LXIX                                                                        1.5+                                                                              0.5+                                                                              1.5+                                                      kg/ha       1+1                                                                               0.5                                                                               1.5                                                                               1.5                                                                               2+1                                                                               1+2                                                 Beta vulgaris                                                                              0  0  0  0  0  0                                                   Avena fatua 95 100                                                                               90 100                                                                               100                                                                               100                                                 Echinochloa crus-galli                                                                     100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                 Stellaria media                                                                            80 90 80 100                                                                               100                                                                               100                                                 Galium aparine                                                                             70 68 70  80                                                                                90                                                                                80                                                 Chenopodium album                                                                          90 80 90 100                                                                               100                                                                               100                                                 Alopecurus myosuroides                                                                     100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                 Lamium amplexicaule                                                                        85 80 85  95                                                                               100                                                                               100                                                 Active ingredient                                                                          I + III + LXIX                                                                 1+ 0.5+                                                                              0.5+                                                                     0.5+                                                                              1+ 0.5+                                                         kg/ha       0.5                                                                               0.5                                                                               1  1+1+1                                                                               2+1+1                                                                               1+2+1                                                                               1+1+2                                      Beta vulgaris                                                                              0  0  0  0    0    0                                               Avena fatua 79 95 75 100  100  100  100                                        Echinochloa crus-galli                                                                     95 100                                                                               96 100  100  100  100                                        Stellaria media                                                                            100                                                                               95 90 100  100  100  100                                        Galium aparine                                                                             100                                                                               80 85 100  100  100  100                                        Chenopodium album                                                                          100                                                                               100                                                                               100                                                                               100  100  100  100                                        Alopecurus myosuroides                                                                     93 100                                                                               98 100  100  100  100                                        Lamium amplexicaule                                                                        90 90 90 100  100  100  100                                        Active ingredient                                                                          I + XXIV + LXIX                                                                1+ 0.5+                                                                              0.5+                                                                     0.5+                                                                              1+ 0.5+                                                         kg/ha       0.5                                                                               0.5                                                                               1  1+1+1                                                                               2+1+1                                                                               1+2+1                                                                               1+1+2                                      Beta vulgaris                                                                              0  0  0  0    0    0    0                                          Avena fatua  87                                                                               100                                                                               85 100  100  100  100                                        Echinochloa crus-galli                                                                     100                                                                               100                                                                               100                                                                               100  100  100  100                                        Stellaria media                                                                            100                                                                               100                                                                               100                                                                               100  100  100  100                                        Galium aparine                                                                             100                                                                               100                                                                               100                                                                               100  100  100  100                                        Chenopodium album                                                                          100                                                                               100                                                                               100                                                                               100  100  100  100                                        Alopecurus myosuroides                                                                     100                                                                               100                                                                               100                                                                               100  100  100  100                                        Lamium amplexicaul                                                                         100                                                                               100                                                                               100                                                                               100  100  100  100                                        Active ingredient                                                                          I + LXI + LXIX                                                     Beta vulgaris                                                                              0  0  0  0    0    0    0                                          Avenua fatua                                                                                87                                                                               95 85 100  100  100  100                                        Echinochloa crus-galli                                                                     100                                                                               100                                                                               100                                                                               100  100  100  100                                        Stellaria media                                                                            100                                                                               90 90 100  100  100  100                                        Galium aparin                                                                               95                                                                               75 80 100  100  100  100                                        Chenopodium album                                                                          100                                                                               100                                                                               100                                                                               100  100  100  100                                        Alopecurus myosuroides                                                                     100                                                                               100                                                                               100                                                                               100  100  100  100                                        Lamium amplexicaule                                                                         90                                                                               85 90 100  100  100  100                                        __________________________________________________________________________       0 = no damage                                                                 100 = complete destruction                                               

EXAMPLE 2

In the greenhouse, various plants were treated at a growth height of from 2 to 15 cm with the following amounts of the following individual active ingredients and compositions thereof as dispersions, emulsions or suspensions:

I -- 1-phenyl-4-amino-5-chloropyridazone-(6)

Iii -- o-(methylaminosulfonyl)-glycolic acid-N-isopropylanilide

Xxiv -- o-(methylaminosulfonyl)-glycolic acid hexamethylene amide

Lxi -- 3-(n-isopropylaminosulfonyloxyacetyl)-3-azabicyclo-(3,2,2)-nonane

Lxix -- 3-methyl-4-amino-5H-6-phenyl-1,2,4-triazin-5-one, each at rates of 0.5, 1, 1.5, 2, 3 and 4 kg/ha,

Iii+lxix, xxiv+lxix and LXI+LXIX -- each at rates of 1+1, 1.5+0.5, 0.5+1.5, 1.5+1.5, 2+1 and 1+2 kg/ha.

After 2 to 3 weeks it was ascertained that, at the lower application rates, the compositions had a better herbicidal action than their components, combined with the same crop plant compatibility. At the higher rates, the compositions had a strong herbicidal action and good crop tolerance.

The results are given below:

    __________________________________________________________________________     Active ingredient                                                                          I             III                                                   kg/ha      0.5                                                                              1 1.5                                                                              2 3  4   0.5                                                                              1 1.5                                                                               2  3  4                                      __________________________________________________________________________     Crop plants:                                                                   Beta vulgaris                                                                               0                                                                                0                                                                                0                                                                                0                                                                                0 10  0  0                                                                                0  0  0 10                                     Unwanted plants:                                                               Avena fatua  5                                                                               13                                                                               15                                                                               25                                                                               40 65 25 50                                                                               60 65 70 72                                     Echinochloa crus-galli                                                                     15                                                                               25                                                                               40                                                                               53                                                                               80 90 45 70                                                                               75 80 90 100                                    Stellaria media                                                                            20                                                                               40                                                                               60                                                                               80                                                                               95 100                                                                                5 15                                                                               25 30 40 50                                     Galium aparine                                                                             20                                                                               40                                                                               50                                                                               70                                                                               80 90 10 15                                                                               20 25 41 45                                     Chenopodium album                                                                          30                                                                               45                                                                               50                                                                               65                                                                               90 100                                                                               10 30                                                                               35 40 45 55                                     Alopecurus myosuroides                                                                      5                                                                               35                                                                               85                                                                               90                                                                               100                                                                               100                                                                               50 90                                                                               100                                                                               100                                                                               100                                                                               100                                    Lamium amplexicaule                                                                        10                                                                               20                                                                               25                                                                               40                                                                               60 85  5 15                                                                               20 25 35 40                                     Active ingredient                                                                          XXIV          LXI                                                  Beta vulgaris                                                                               0                                                                                0                                                                                0                                                                                5                                                                               10 15 0   0                                                                                0  0  0  5                                     Avena fatua 30                                                                               45                                                                               60                                                                               70                                                                               80 95 20 40                                                                               55 65 78 85                                     Echinochloa crus-galli                                                                     40                                                                               70                                                                               80                                                                               90                                                                               98 100                                                                               25 60                                                                               80 90 100                                                                               100                                    Stellaria media                                                                            20                                                                               40                                                                               45                                                                               60                                                                               70 85 0  10                                                                               20 30 50 60                                     Galium aparin                                                                              20                                                                               35                                                                               40                                                                               50                                                                               65 75 0   5                                                                               10 15 40 50                                     Chenopodium album                                                                          15                                                                               25                                                                               35                                                                               45                                                                               60 80 5  10                                                                               15 25 40 50                                     Alopecurus myosuroides                                                                     50                                                                               75                                                                               90                                                                               95                                                                               100                                                                               100                                                                               50 80                                                                               90 95 100                                                                               100                                    Lamium amplexicaule                                                                         5                                                                               20                                                                               35                                                                               45                                                                               55 60 0   5                                                                               15 20 30 50                                     Active ingredient                                                                          LXIX                                                               kg/ha       0.5                                                                               1  1.5                                                                               2  3  4                                                   Beta vulgaris                                                                               0  0  0  0  0  0                                                  Avena fatua 20 40 60 80 90 95                                                  Echinochloa crus-galli                                                                     30 60 70 85    100                                                 Stellaria media                                                                             0 10 20 30    60                                                  Galium aparine                                                                             15 30 40 55 70 90                                                  Chenopodium album                                                                          20 35 50 70 85 95                                                  Alopecurus myosuroides                                                                     30 50 65 80 100                                                                               100                                                 Active ingredient                                                                          III + LXIX        XXIV + LXIX                                                     1.5+                                                                              0.5+                                                                              1.5+        1.5+                                                                              0.5+                                                                              1.5+                                    kg/ha       1+1                                                                               0.5                                                                               1.5                                                                               1.5                                                                               2+1                                                                               1+2                                                                               1+1                                                                               0.5                                                                               1.5                                                                               1.5                                                                               2+1                                                                               1+2                               Beta vulgaris                                                                              0  0  0  0  0  0  0  0  0  0  5  0                                 Avena fatua 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                               Echinochloa crus-galli                                                                     100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                               Stellaria media                                                                            100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                               Galium aparine                                                                              85                                                                                76                                                                                90                                                                               100                                                                                95                                                                               100                                                                               100                                                                                95                                                                               100                                                                               100                                                                               100                                                                               100                                Chenopodium album                                                                         100                                                                                95                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                                95                                                                               100                                                                               100                                                                               100                                                                               100                               Alopecurus myosuroides                                                                     100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                               Lamium amplexicaule                                                                        100                                                                                85                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                               Active ingredient                                                                          LXI + LXIX                                                                        1.5+                                                                              0.5+                                                                              1.5+                                                      kg/ha       1+1                                                                               0.5                                                                               1.5                                                                               1.5                                                                               2+1                                                                               1+2                                                 Beta vulgaris                                                                              0  0  0  0  0  0                                                   Avena fatua 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                 Echinochloa crus-galli                                                                     100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                 Stellaria media                                                                            100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                 Galium aparine                                                                              75                                                                                67                                                                                80                                                                                90                                                                                85                                                                               100                                                 Chenopodium album                                                                           85                                                                                75                                                                                95                                                                               100                                                                               100                                                                               100                                                 Alopecurus myosuroides                                                                     100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                 Lamium amplexicaule                                                                         95                                                                                85                                                                               100                                                                               100                                                                               100                                                                               100                                                 __________________________________________________________________________       0 = no damage                                                                 100 = complete destruction                                                

I claim:
 1. A herbicide composition comprising an inert carrier having dispersed therein a herbicidally effective amount of a mixture consisting essentially of(a) O-(methylaminosulfonyl)-glycolic acid-N-isopropylanilide, O-(methylaminosulfonyl)-glycolic acid hexamethylene amide, or 3-(N-isopropylaminosulfonyloxyacetyl)-3-azabicyclo-(3,2,2)-nonane, and (b) 3-methyl-4-amino-5H-6-phenyl-1,2,4-triazin-5-one in a weight ratio of 3:1 to 1:3. 